CHEBI:29650 - narbonolide

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ChEBI Name narbonolide
ChEBI ID CHEBI:29650
Definition A 14-membererd macrolide containing seven stereocentres carrying one ethyl, one hydroxy and five methyl substituents. It is the aglycone of the antibiotic narbonomycin and an intermediate in the biosynthesis of pikromycin.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H32O5
Net Charge 0
Average Mass 352.46510
Monoisotopic Mass 352.22497
InChI InChI=1S/C20H32O5/c1-7-17-11(2)8-9-16(21)12(3)10-13(4)18(22)14(5)19(23)15(6)20(24)25-17/h8-9,11-15,17-18,22H,7,10H2,1-6H3/b9-8+/t11-,12-,13+,14-,15-,17-,18+/m1/s1
InChIKey YFFOFFWSBYZSOI-HQWJGCFGSA-N
SMILES CC[C@H]1OC(=O)[C@H](C)C(=O)[C@H](C)[C@@H](O)[C@@H](C)C[C@@H](C)C(=O)\C=C\[C@H]1C
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing narbonolide (CHEBI:29650) has role metabolite (CHEBI:25212)
narbonolide (CHEBI:29650) is a enone (CHEBI:51689)
narbonolide (CHEBI:29650) is a macrolide (CHEBI:25106)
Incoming narbomycin (CHEBI:29649) has functional parent narbonolide (CHEBI:29650)
neopikromycin (CHEBI:85614) has functional parent narbonolide (CHEBI:29650)
novapikromycin (CHEBI:77648) has functional parent narbonolide (CHEBI:29650)
pikromycin (CHEBI:29665) has functional parent narbonolide (CHEBI:29650)
IUPAC Name
(3R,5R,6S,7S,9R,11E,13R,14R)-14-ethyl-6-hydroxy-3,5,7,9,13-pentamethyloxacyclotetradec-11-ene-2,4,10-trione
Synonyms Sources
Narbonolide KEGG COMPOUND
narbonolide UniProt
Manual Xref Database
C11997 KEGG COMPOUND
View more database links
Registry Number Type Source
4541269 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
16122247 PubMed citation Europe PMC
17168607 PubMed citation Europe PMC
18205385 PubMed citation Europe PMC
4792390 PubMed citation Europe PMC
Last Modified
29 April 2015